Methyl iodide → 4-(Dimethylamino)-N,N,N-trimethylanilinium iodide

HRID 1500127Notes

Reaction equation

HRID 1500127 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=1.C[I:14].[CH2:15](Cl)Cl>ClC(Cl)C>[I-:14].[CH3:10][N:9]([CH3:11])[C:6]1[CH:7]=[CH:8][C:3]([N+:2]([CH3:15])([CH3:12])[CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 7490N1,N1,N4,N4-tetramethyl-1,4-Benzenediamine

Product 1

HCID 448873084-(Dimethylamino)-N,N,N-trimethylanilinium iodideYield 70%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

N,N,N′,N′-Tetramethyl-benzene-1,4-diamine (200 mg, 1.22 mmol) was dissolved in dichloroethane (2 mL) and methyl iodide (173 mg, 1.22 mmol) was added dropwise. The reaction was refluxed for 1 hour, cooled to room temperature, the solid filtered out, washed with dichloromethane, dissolved in methanol and purified via flash column chromatography using a gradient of 0-8% MeOH:DCM to give 260 mg of grey solid (70% yield). 1H NMR (DMSO-d6): δ7.67 (d, J=9.3, 2H), 6.77 (d, J=9.3, 2H) 3.49 (s, 9H), 2.92 (s, 6H); MS (ESI, m/z): 179 (M+).

Workup

  1. temperatureThe reaction was refluxed for 1 hour
  2. filtrationthe solid filtered out
  3. washwashed with dichloromethane
  4. dissolutiondissolved in methanol
  5. custompurified via flash column chromatography

Sources & evidence

ORD record
ord-841b35821f364d479505934f00e9d528
Source dataset
uspto-grants-2015_12
Patent number
US09205156B2

Reaction notes

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